My instinct on seeing them fishing before Jack said anything was to assume Bobby was more the sort of dad who would have taught them to fish just based on 7×09/10 and the final retconning done to prove Bobby had “always” been the more attentive father and give him a sort of check mate to John… But Jack’s comment to me seems to make it too obvious to not think that they really are talking about John, because his legacy is all over Dean and Jack’s relationship. There’s something so grim about everything to do with them, that I’m just constantly simmering in low-key horror every time they interact (so I’ve been absolutely living for the last 2 episodes :P) and I think it is to explore the left over trauma John gave Dean in what Dean now deals out to Jack, or how they DON’T follow in the same toxic paths. Dean teaches Jack to drive after deciding he’s around 18-19 based on the birth year he spitballs at the hospital, and so unlike how he learned to drive when he was in single digits so that he could ferry them around in an emergency, Jack is getting adult rite of passage stuff with Dean.
I think the typical fishing with dad age in the tropes is like, 10 onwards and early teen, sort of initial adult bonding with the son as well… Kids much younger than that dont have as much attention span and my vague impression of the trope is of a manhood ritual that fathers take on themselves. It’s probably likely John taught Dean when he was pretty young just because he was forced into everything young, but I think it is important that this reminds us there WERE good times, just that the story focuses on the tragedy. I think John and Dean probably did fish together at least a few times and it probably was this manly quiet bonding time where they had intermittent conversation, caught some fish, and felt all manly and Dean felt all grown up and awesome. Fishing seems to be about catching a moment of peace and quiet and it’s a good thing both for Jack to do here and also as a memory for Dean of John which really shows a nice quiet moment to illustrate when things could be good.
Like I said in my notes, though, like with Mary having to clarify for Sam that a nice John is her John, Jack clearly sees that the fishing was a one good moment in a sea of awful with Dean and John and he wants this experience with Dean BECAUSE it was a good time and stands out amongst that. It doesn’t have to be redemptive of your image of John, but I think it’s interesting that because they’ve been serving us this story for so long about how John was such a poor father, and because it’s all high stakes drama until these last couple of seasons where things can slow down and breathe, we rarely get much context of why they would ever like John’s memory at ALL.
Dabb also wrote 10×09 with the reminiscing about John saving Dean when he was roofied at that club, and it was way more complicated in the dynamic and giving us a lot to debate about when it came to how John had handled it and so on, but again it was presented as them having a good memory of John to share and feel that he wasn’t all bad.
It comes across to me like a healing process for Dean to be able to teach HIS son to drive and to fish with him, and despite the tragedy, their dynamic is healthier and things are coming across much better than how Dean was raised and that’s very obvious underneath it that Dean is giving Jack a better time and being a better father, but also walking in John’s footsteps as he does so. Sort of like… Each step along the way, healing something that might feel bad about John with doing it better with Jack, perhaps…
I liked that Dean suggested a hook up and Jack flat out refused with a better idea for their own personal bonding… It was very different from 5×03 and Dean trying to give Cas the ~human experience~ of course, but also there’s a real sense that Jack is rejecting all the associated sadness and toxic masculinity/coping mechanisms etc in Dean’s hook up habit and choosing a more wholesome activity. And again that reflects back on Dean that he didn’t take Jack to get some momentary pleasure where obviously it wouldn’t even really be bonding between them any more, it would just be forcing Jack through a rite of passage to ~make a man of him~ in a way where I can see John almost approving of Dean having hook ups from when he was about the age he reckons Jack presents as in this same way Dean is working through a natural assumption of what someone would want/what a boy is supposed to do. But Jack isn’t here for that, he has limited time in his mayfly life and he knows what he wants, which is WHOLESOME father/son bonding and that involves inherently rejecting some of the worse aspects of the emotional landscape Dean was raised in.
And also just that Jack can ASK for this affection and get Dean to give him the same experience as his happiest memories with John, while I imagine for Dean it was 100% guided by John to decide when and where they would fish, as Dean inherently had a subordinate relationship to John, which Jack doesn’t have with Dean despite the obvious son/father relationship they do have and the way Dean does care for him and guide him now.
… This ended up a longer ramble than I meant but I am so utterly in love with Dean having a son and it not playing out like Ben, but that by coming to him from the other direction, not that he was some precious thing that could be broken, but discovering that Jack wasn’t a monster and finally seeing himself in Jack, that it’s unlocked the ultimate version of Dean’s nurturing side which we’ve been getting only glimpses of for so many years :’)